The 1160 licensed to Florence will always be subject to interfering skywave, and have marginal coverage during fringe daytime hours. It's protective area for nighttime coverage doesn't reach Covington. It's not just Chicago you deal with. You can put all the copper you want in the ground, you can't change physics. It wasn't meant to service northern subs in Cinti. It's a northern KY channel. Always will be.
A translator won't make much difference for what we hear on 1160. I like Dennis Miller, but it's pretty poor audio coming through my speaker. Not sure what happened but sounds like the station is broadcasting through a shower stall. Like cheap sounding reverb. Clean up your audio and maybe you can cut through the static up here in the north.
WLW has crapped up the highest fidelity station ever with that digital noise, and 55 sounds like a buzz saw...so 1160 has competition for some of the worst audio.
Sad.